Hydroxyamine hydrochloride → 3-Azetidinecarboxylic acid, 1-[4-[(hydroxyimino)methyl]phenyl]-, methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)[CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[NH2:23][OH:24]>CO.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[N:23][OH:24])=[CH:11][CH:10]=2)[CH2:6]1)=[O:4]Participants
Procedure
To a stirred suspension of 1-(4-formyl-phenyl)-azetidine-3-carboxylic acid methyl ester (Preparation 9, 2.6 g, 11.87 mmol) in methanol (25 mL) and water (25 mL) was added sodium acetate (1.75 g, 21.36 mmol) followed by hydroxylamine hydrochloride (1.24 g, 17.80 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 3 hours. After consumption of starting material, methanol was evaporated under reduced pressure and extracted with EtOAc (4×30 mL). Combined organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to afford yellow colored solid (2.86 g, 99%). 1H NMR (400 MHz, CDCl3) δ: 3.55-3.59 (m, 1H), 3.75 (s, 3H), 4.05-4.13 (m, 4H), 6.42 (d, 2H, J=8.56 Hz), 7.41 (d, 2H, J=8.6 Hz), 8.03 (s, 1H); LC-MS (M+H): =235.00.
Workup
- customResulting
- customreaction mixture
- customAfter consumption of starting material, methanol
- customwas evaporated under reduced pressure
- extractionextracted with EtOAc (4×30 mL)
- dry with materialCombined organic layer was dried over anhydrous sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-eab8c6b79e4c47a8bfac0ab4da12e76e
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09061013B2
Reaction notes
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